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The original version features legendary Black Sabbath singer Ozzy Osbourne on lead vocals. A pre-fame Madonna had auditioned for the vocal but was not used on the final release. In 1992, it was re-recorded and remixed by house music producer Steve "Silk" Hurley, and features actressKim Basinger alongside a re-recorded Ozzy Osbourne on vocals. It appeared on the group's compilation album, Hello Dad... I'm in Jail. The original plan was to restore Madonna's vocals to the track for the re-release, but the artist refused to grant permission, hence actress Kim Basinger was approached instead. However, Madonna's restored vocals were accidentally released on two occasions. A full Madonna vocal appears on the 2LP and double cassette formats of compilation release Now Dance 92, entitled 12" Mix. The CD format of this compilation includes the regular 7" Mix, however. Secondly, on the 12" and CD single formats of Was (Not Was)'s follow up single, "Somewhere in America (There's a Street Named after My Dad)", there is a Dub Mix of "Shake Your Head" which uses several of Madonna's vocals. Although the song did not chart in the US, it was the band's biggest commercial success across the Atlantic, reaching #4 in the UK charts.

There are several versions of the 1992 remake: The 3:48 single version starts with Ozzy Osbourne singing "You can't feed the hungry, you can't talk Shakespeare to a monkey..." The 4:00 album version starts with female vocals (presumably Kim Basinger) singing "You can't argue with death. You can't break a burly sailor's neck. You can't drink lava from plastic glasses...". There is also a Steve "Silk" Hurley 12" Mix and a 12" Dub.

The song's lyrics deal with things that cannot be done (some are outlandish, some can be done, but have a high amount of difficulty). After Basinger and Osbourne detail these things, the chorus comes in with the title hook.